Synthesis of sugar-derived phostones by activation of γ-hydroxyphosphonic acids

被引：11

作者：

Bosco, M

Bisseret, P

Eustache, J

机构：

[1] Univ Haute Alsace, CNRS, Lab Chim Organ & Bioorgan, F-68093 Mulhouse, France

[2] Univ Haute Alsac, Ecole Natl Super Chim Mulhouse 3, F-68093 Mulhouse, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(03)00240-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of carbohydrate-derived gamma-hydroxyphosphonic acids under usual acetylation conditions affords the corresponding phostones in good yield. The method could be used for the preparation of free phostones as well as alpha- and beta-phosphonomethylarabinose. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2347 / 2349

页数：3

相关论文

共 11 条

[1]

Billault I, 1999, HELV CHIM ACTA, V82, P1137, DOI 10.1002/(SICI)1522-2675(19990804)82:8<1137::AID-HLCA1137>3.3.CO

[2]

2-E

[3] Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-alpha-D-glucosamine 1-phosphate and N-acetyl-alpha-D-mannosamine 1-phosphate [J].

Casero, F ;

Cipolla, L ;

Lay, L ;

Nicotra, F ;

Panza, L ;

Russo, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3428-3432

[4] Synthesis and antituberculosis activity of C-phosphonate analogues of decaprenolphosphoarabinose, a key intermediate in the biosynthesis of mycobacterial arabinogalactan and lipoarabinomannan [J].

Centrone, CA ;

Lowary, TL .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8862-8870

[5] SYNTHESIS OF ISOSTERIC PHOSPHONATE ANALOGS OF SOME BIOLOGICALLY IMPORTANT PHOSPHODIESTERS [J].

JONES, GH ;

ALBRECHT, HP ;

DAMODARAN, NP ;

MOFFATT, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5510-+

[6] SYNTHESIS OF C-ARABINOFURANOSYL COMPOUNDS - PHOSPHONATE AND CARBOXYLATE ISOSTERES OF D-ARABINOSE 1,5-BISPHOSPHATE [J].

MARYANOFF, BE ;

NORTEY, SO ;

INNERS, RR ;

CAMPBELL, SA ;

REITZ, AB ;

LIOTTA, D .

CARBOHYDRATE RESEARCH, 1987, 171 :259-278

[7] Formation of phostonic acids during the reduction of azidonucleosidephosphonic acids [J].

Morr, M ;

Kakoschke, C ;

Ernst, L .

TETRAHEDRON LETTERS, 2001, 42 (50) :8841-8843

[8] Synthesis and biological evaluation of 1',2'-seconucleo-5'-phosphonates [J].

Racha, S ;

Vargeese, C ;

Vemishetti, P ;

ElSubbagh, HI ;

Abushanab, E ;

Panzica, RP .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1130-1135

[9] Polyprenylphosphate-pentoses in mycobacteria are synthesized from 5-phosphoribose pyrophosphate [J].

Scherman, MS ;

KalbeBournonville, L ;

Bush, D ;

Deng, LY ;

McNeil, M .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (47) :29652-29658

[10]

WOLUCKA BA, 1994, J BIOL CHEM, V269, P23328